Undecided
by jr forever
Summary: What would have happened if Rory and called or written a letter to Jess while she was in Washington? I didn't really like how season 3 started with Jess dating Shane and Rory still with Dean so I decided to write it my way. This is my first fanfic so be n
1. Chapter 1

**Undecided:**

Ch.1

'_Did that really just happen? Did I really kiss Jess? What was I thinking? I mean, it was amazing, and I've wanted to do that for awhile now but_…' "Whoa! Did I just think that?" Rory mumbled to herself. She didn't know where that thought had come from. Jess and her were just friends, weren't they? "Of course we are. We're just friends, nothing more." She whispered, trying to convince herself that she felt nothing for Jess. _'I can't like Jess. I'm with Dean, my really nice, loving, considerate boyfriend that I love. Oh God! Dean! How could I have done that to him? How could I have cheated on him? He's going to be so hurt when he finds out. How am I going to explain this to him? Um, hi Dean. While you were talking to my mom, Lane, and the rest of Stars Hollow, I was kissing Jess, the guy you hate!'_ Rory thought sarcastically. _'Oh yeah, like that's really gonna work.'_

Just then she reached Lorelai at the bridge. Lorelai immediately handed her a bouquet and Rory told her, "I think I'm going to Washington." She hadn't been sure about going before, but now after that kiss with Jess…She had to get out of there. It wasn't like she hadn't enjoyed it, because she had. She just didn't know how she was going to face him again. Plus there was the whole Dean thing. Just thinking about the kiss she had shared with Jess made her feel guilty. She knew she had to tell Dean, but she didn't want to hurt him.

"Okay." Lorelai mumbled as they walked over the bridge and down the aisle to watch Sookie and Jackson get married.

"Are you sure you want to do this?" Lorelai asked Rory as they waited for her to board her plane.

"Yeah…It's not like I really have a choice anyway. Paris would kill me if I didn't go to Washington with her this summer."

"True and then I'd never be able to talk to you again…Unless you turned into a ghost and haunted our house. But then everyone would think I was crazy for talking to you when your dead and they would probably-"

"Put you in a mental institution?" Rory interrupted, putting an end to her mother's crazy rambling. She knew what she was trying to do and she loved her even more for it. They had both been a little depressed since Sookie's wedding. "Are you sure you're okay? After everything that's happened…"

"Yeah kid. I'm fine."

"I still can't believe dad did that to you! Who does he think he is? Showing up in our lives, and giving us false hope. You know, I actually believed him. I thought that we would finally be a family, and then he went and pulled this."

"Rory, Hun, calm down. Don't let this ruin your trip to Washington. You're going to go and you're going to have a really good time showing those smart kids what you're made of."

"Okay. I guess you're right. I love you mom."

"I love you too." _'How am I going to survive the next six weeks without Rory?'_ Lorelai thought as they hugged each other tightly.

"Um, I think that's my flight."

"I'm gonna miss you Hun."

"I'm gonna miss you too."

"Be safe!"

"I will." Rory called out as she turned and boarded her plane.


	2. Chapter 2

**Undecided:**

**Disclaimer: I don't own Gilmore Girls.**

Ch.2

Rory sat in the dorm room that she shared with Paris two weeks later wondering what she should do. She knew she had to talk to Jess about the kiss at Sookie's wedding, but she didn't know how. Every time she thought about what that conversation would be like she would blush in embarrassment. What do you say to someone after you kiss them while you still have a boyfriend? She thought about calling him, but didn't want to risk hearing the regret in his voice. The kiss had probably meant nothing to him. Why would someone like him want to be with her? He could have girl he wanted.

After sitting there thinking about this for a couple of hours she decided to write him a letter:

_Dear Jess,_

_I don't really know how to start this, but do you remember the kiss at _

_Sookie's wedding?_

"This is stupid." Rory said, crumbling the paper and throwing it in the trash can. She was about to pull out another piece to start again when the door burst open and Paris came in.

"Red, purple, green. Where the hell is it?"

Rory pulled out another piece of paper and was just about to start writing when Paris said, "Hey, Stop doing whatever it is that you're doing. I need help here."

Rory reluctantly put the paper aside to see what Paris needed help with. Once she turned around and took in her appearance she remembered that Paris had a date that night.

"That's it I'm shaving my head."

"Okay. Paris, you have got to calm down." Rory said while getting up and calmly walking over to Paris.

"I had a black sweater, and now it's gone." Paris said while trying to put her hair in a pony tail.

"I'm not just talking about right now. In general, you need to calm down."

"He's almost here. I'm not dressed, my makeup's not done, and I haven't gone through the _Zagat_ to pick out a restaurant."

"Why don't you just let him pick the restaurant?"

"What if he doesn't have a _Zagat_?"

"Then he'll wing it."

"Wing it? How come other girls get planned-out dinners, flowers, candy, rose petals thrown on the floor and I get "wing it"?

"Well you don't know that you got "wing it"?

"No, I do. I've got "wing it". I can't do this."

"What?"

"Date. I can't date. I'm not genetically set up for it.

"That's not true."

"I get no pleasure out of the prospect of the preparation. I'm covered in hives. I've showered four times. And for what? Some guy who doesn't have the brains to buy a _Zagat_ so we don't wind up in a restaurant that was really just a front for a cocaine-laundering ring?

"Sit."

Paris reluctantly sat down. "It's a dare. He was dared to take me out. I bet Trent Lott was behind this."

"Trent Lott did not dare Jamie to take you out." Rory said while sitting down next to Paris and helping her with her make-up. "Close. Jamie likes you. He asked you out because he likes you. Now look up."

"Maybe I shouldn't go. I mean what if I fall for him and he doesn't like me?"

"Then you'll find someone else."

"But what if there is no one else?"

"Then you'll buy some cats."

"I wish I knew if he was right for me. You know? So I don't put myself through all of this for nothing. I mean women fall for men who are wrong for them all the time. And then they get sidetracked from their goals. They give up careers and become alcoholics. And if you're Sunny von Bulow, wind up in a coma completely incapable of stopping Glenn Close from playing you in a movie."

"I think you should wear your hair down." Rory said while getting up and going behind Paris to do her hair.

"How do you know if a guy is right for you?"

"You just have to feel it."

"All I feel is my back breaking out."

"You'll know, okay? You just have to let it happen. And then, probably when you're not looking you'll find someone who complements you."

"Meaning?"

"Someone who likes what you like. Someone who reads the same books or listens to the same music, or likes to trash the same movies. Someone compatible." The only person Rory could think about while she said this was Jess. She had just described him and their relationship.

"Okay."

"But not so compatible that they're boring." As Rory said this she thought about Dean. She couldn't remember the last time that they had really had fun together. Usually when they hung out she was bored out of her mind. She liked to talk about books, movies, music, etc. Dean didn't. He thought all of these things were extremely boring and preferred watching 'The Lord of The Rings' a trillion times. It was then that she realized what she had to do.

"Someone who's compatible but not compatible."

"Yeah, kind of. I mean you respect each other's opinions, and you can laugh at the same jokes, but I don't know there's just something about not quite knowing what the other person's gonna do at all times. It's just really exciting."

Paris looked up at Rory and smiled. She knew who Rory was describing: Jess. She may not have known him for long, but she knew that they had a lot in common, and that they both had feelings for each other. She just wondered how long it would take them to realize that.

"Look, just have a good time. You'll figure it out." Rory said while picking up a black sweater.

"Yeah, I hope I figure it out fast before I throw up." Paris replied, putting on the sweater that Rory had found.

Before they could say another word they heard a knock on the door. "That's him. Turn around." Rory said, inspecting her work.

"Well?"

"Perfect."

"Promise?"

"Swear."

"Thanks. Now get in the closet."

"What?"

"If he comes in here and sees you, he won't want to date me anymore."

"Paris, that's crazy. He's seen me for two weeks."

"Yes, in conferences, crowded lecture halls, badly-lit banquet rooms with crappy food smells. Not at night when it's dating time and he's thinking about dating, and you look all datable."

"I'm not looking datable."

"Please. I can't risk it. At least if there's nothing to compare me to then I've got a fighting chance. Please."

"Okay." Rory reluctantly replied. "But when you get home, you need to get a new therapist because the one you have is really not working." Rory said all of this while walking across the room, picking up a notebook and a flashlight, and going into the closet.

Once the closet door was shut Paris said, "Thanks for helping me get ready."

"Any time." Rory said hoping Paris and her date would leave soon. She had a lot to think about. _'I can't believe it took me so long to realize that I like Jess. Not like that realization will help me. Just because I like him doesn't mean he likes me. And even if he did, I wouldn't be able to be with him until I broke up with Dean. Wait. Where are all of these thoughts coming from? I can't break up with Dean. I love him. Don't I?'_ Rory sat there in confusion for the next hour or so before she realized that she had been lying to herself. She didn't love Dean. She never really had. She had just loved the thought of him. I mean who wouldn't. He was really nice, considerate, and the perfect first boyfriend, but he wasn't the guy for her.

With that thought in mind she opened up the notebook and began to write:

"_Dear Jess,_

_Wow! I really don't know what to say. What do you say to someone after you kiss them while you have a boyfriend…I guess I should just be honest. Do you remember the kiss at Sookie's wedding? I sure do. I know that you're probably expecting me to apologize, but I can't. You see, I enjoyed it. And I'm not sorry that it happened. I'm just sorry that it happened under the circumstances that it did (with me still being with Dean.) But you won't have to worry about that for long. I plan to break up with him as soon as I get back to Stars Hollow. I don't know how I will, but I will. Is there any way to break up with someone without hurting them? Because I really don't want to hurt him. He's always been there for me, and he doesn't deserve to get hurt. Not by me…But enough about Dean. Dean isn't the point of this letter. You are. You see I like you, a lot. I have for a long time. I was just too scared to admit it. But I'm admitting it now: I like you Jess Mariono. I know that you probably don't feel the same way about me, but I thought you should know. I just hope that you knowing this won't affect our friendship if you don't feel the same._

_Rory _

After Rory finished the letter she got out of the closet, put it in an envelope, grabbed her car rental keys, and went to the nearest post office. She knew that if she didn't send it now then she never would. _'I just hope this doesn't make things worse.'_ Rory thought as she put it in the mail box and drove back to the convention.


	3. Chapter 3

**Undecided:**

**Disclaimer: I don't own Gilmore Girls or anything related to it.**

**Just so you know I used lines from the episode: Lazy-Hazy-Crazy Days in this chapter.**

Ch.3

_Four Weeks Later:_

Rory was abruptly awoken by the annoying sound of a phone ringing. She rolled over and wearily answered it. "Hello?" She said still half asleep.

"You have to come home."

"Mom?"

"You're gone and the house is quiet. Bill Maher is canceled. The name of the show was _Politically Incorrect_. Didn't anyone read the title? He was supposed to say those things!"

"You had another dream."

"Yes."

"The doctor is in." Rory said while she sat up.

"Okay, I'm lying in bed and I'm sleeping. I'm wearing this fabulous nightgown. And like 30 alarm clocks go off. And so I get out of bed and I walk downstairs. And there, standing in the kitchen, is Luke."

"Was he naked?"

"No. He was making breakfast."

"Naked?"

"You've been in Washington way too long."

"Sorry. Go ahead. He was making breakfast."

"Eggs and pancakes and bacon. And he put decaf coffee in my regular coffee bag which, of course, I knew immediately."

"Hi. The nose."

"Exactly. So eventually I find the real stuff under the sink. He hands me my breakfast, and then…"

"What?"

Lorelai took a deep breath and said, "He kissed me and talked to my stomach!"

"Why would he do that?"

"Because apparently I'm pregnant."

"What?"

"With twins!" It was quiet for a couple of seconds. Finally Lorelai couldn't take the silence anymore and said, "Say something."

"You are going to be so fat."

"Just analyze my dream, please."

"Okay. Well your dream is telling you that you are secretly in love with Luke, and you want to marry him, and have his twins."

"Uh, no. Try again."

"What do you mean try again? You asked me to analyze your dream. And I analyzed your dream."

"Yes. Well, I reject that analysis. So I'd like another one, please."

"You can't just reject an analysis and try again. You're not shopping for bathing suits here."

"Give me another analysis or I'll put your Taylor hula-hooping dream into a whole other context."

"I told you Taylor was supposed to be Dean. I could tell by his freakishly thick head of hair."

"I'm waiting."

"Okay, maybe you're still upset about what happened with Dad and you're jealous of Sherry because she's having his baby and not you…Mom?"

"I miss you." Lorelai said on the verge of tears.

"I miss you too."

"Woodward. Bernstein. Harry Thomason."

"Is that Paris?"

"Yeah, she talks in her sleep. Long in-depth arguments. I'm glad I only have one more day here."

"Me too. What do you have on your agenda for tomorrow? Or today, actually.

"We have a breakfast mixer with members of Congress and the Senate."

"Cool. See if you could steal me something off of Tom Daschle's fruit plate."

"I'll see what I can do."

"See you Friday, Doc."

"See you Friday." After hanging up the phone Rory went back under the covers and tried to go back to sleep only to hear the words, "I did not have sexual relations with that woman." come from Paris' mouth. _'This is going to be a long night.'_ Rory thought as she rolled over.

**Friday at 3:00 p.m.**

Not even a second after Rory got off her plane she heard a voice say, "Hey, Gilmore!"

She looked over and saw her mom standing on the other side of the room. "Mom!" She said as they ran to each other and hugged, dropping their bags in the process, which caused them to trip over each other and land in an ungraceful heap on the floor. They both laughed uncontrollably.

"Luckily there are video cameras everywhere that caught that very graceful moment on tape." Lorelai said as she righted one of her bags.

"I'm so glad to see you."

"I'm glad to see you."

"I'm never leaving home again."  
"Oh, that's my emotionally-stunted girl! Hey I got you gifts." Lorelai said while reaching into one of the bags.

"What? I'm the one that left town. I'm supposed to get you gifts."

"Ah, well I got here early and there was nothing to do except feed Gummi Bears to the bomb-sniffing dogs which apparently the United States government frowns upon."

"You got in trouble with the government while you were waiting for me?"

"Just a little."

"How much is a little?

"Learn Russian. Okay, here you go." Lorelai said while handing Rory something.

"Wow! A Hartford, Connecticut sweatshirt."

"Nice, huh?"

"Hartford Connecticut notebook, Hartford Connecticut pencil set, Hartford Connecticut shot glass-"

"And beer bug." Lorelai said enthusiastically.

"Hartford baguette, Harford bear, Hartford sunglasses."

"You like?"

"I love."

"Alright let's go. We'll get your bags, then we'll hit the road and then I can't wait to hear all about Washington. And by the way, I got you out of dinner with the Gilmore's tonight. I thought you and Dean might enjoy a little Peaches and Herb time together."

"Oh…Thanks. What did you tell them?"

"That you get home tomorrow."

"Big fat lie."

"Yes, which proves how much I love you. The fact that I was willing to lie to my own parents who I never lie to just so you could have a night of happiness is proof of the deep, undying devotion that I have for you."

"I appreciate that."

"And all that devotion could be yours for the low price of $29.95."

"Forget it." Rory said turning her head and not looking her mother in the eye.

"Okay. I'll throw in a set of steak knives."

"My bags, please." Rory said in exasperation. She didn't like the fact that her mom had lied to Emily and Richard. It just didn't settle right with her. She really appreciated the fact that she had a Friday off, but she would actually rather have dinner with her grandparents then spend time with Dean. She didn't want to see his face when she broke up with him. She didn't want to hurt him, but she knew that she would, which was why she wanted to avoid it for as long as possible.

"Are you telling me that you want this gesture of my love for free? What kind of world are you living in?"

"Oh my God. You do know one option was leaving some of your books at home?" Lorelai said as the entered their house.

"Hey I offered to carry that one."

"Next time don't offer, insist. Look I'm lopsided now." Lorelai said as she demonstrated this by walking around tilting her shoulders to the right so one would be higher then the other.

"I can't believe I'm home. I feel like I've been away forever."

"I agree."

"Hello, living room."

"Hello, Rory. We missed you." Lorelai said in a funny pitched voice. "Not the ottoman, of course, but everyone knows he's a snob. Napoleon complex. He only really likes the magazine rack."

"My God. I missed everything." Rory said while walking around the house.

"My kitchen, my room, my books, my CD's, my stuff. Where's my pillow?" Rory said after walking in her room and putting her stuff down.

"What?"

"You took my pillow."

"I did not take your pillow."

"You waited until I left, you went into my room, and you took my pillow."

"Well you weren't using it."

"What else did you take?" Rory said while walking into her room to see if anything else was missing.

"Nothing. Your comforter came into my room by itself. It brought your Bauhaus T-shirt with it."

"I want my stuff back by tomorrow morning."

"Just 'cause you leave doesn't mean the world stops."

"By noon."

"Fine." Lorelai said while listening to the answer machine.

"_Lor, it's me. Please just call."_ Lorelai didn't wait to listen to anymore. She deleted the message without a second thought.

"Dad?" said Rory, walking out of her room.

"Yeah."

"You still haven't talked to him yet, huh?"

"No. You?"

"Nope."

"He's called."

"Yup, I know. He's called me too."

"I just I- I don't really know what to say.

"How long are you gonna freeze him out for?"

"I don't know."

"Right."

"You?"

"I don't know either."

"I have to tell my parents tonight." Lorelai said seriously.

"Are you sure you don't want me to go with you and I don't know, distract them?"

"No. You've got Dean coming over. I'll be fine. I'll bring them something shiny."

"Okay." Before Rory could say anything else the phone rang. "Hello?" she answered.

"Hey." It was Dean.

"Hi, Dean."

"Are you home?"

"Yeah. I just got here."

"Good…I missed you." The line was silent for a couple of minutes. "So, are we still on for tonight?"

"Yup. My house at 6:00" Rory said in a strained voice. _'How am I going to break up with him without hurting him? Is that even possible?'_

"Okay, sounds good. I'll see you later."

"Yeah, later."

"I'm really glad your home Rory."

"Yeah, me too."

"I love you."

"You too." Rory answered. She couldn't bring herself to say the words, but Dean didn't notice. They hung up a minute later with plans for him to come over for a movie marathon.


	4. Chapter 4

**Undecided:**

**Disclaimer: I don't own Gilmore Girls or anything related to it.**

**Sorry I didn't update yesterday. I was really busy. I took my drivers test, and finally got my license. Yay! Anyways this chapter was really hard to write. I hope you like it…Jess will be in it really soon. **

**Ch.4**

_5:30 that night:_

_'What am I going to do? Dean is supposed to be here in thirty minutes! How am I going to break up with him? Should I just come right out and say it, or should I wait until after the movies? What should I say? What do you say to someone when you want to break up with them?'_ Rory was brought out of her thoughts by a knock at the door. _'Please don't be Dean. I'm not ready to see you yet.'_

"Dean…You're early." Rory said in a strained voice.

"Yeah, well. I couldn't wait to see you. You don't mind do you?"

"No. Not at all." Rory said, lying through her teeth. She had wanted more time to think everything through, and figure out a way to break up with Dean without hurting him too badly.

"I missed you." Dean said, completely oblivious to her struggle.

"I missed you too." Rory said sincerely. She had missed him, just not the way he had missed her. Rory started to panic when she saw Dean lower his head to lean in and kiss her. She couldn't let him kiss her. Not now. Not when she was about to break his heart.

Rory turned her head away a second before his lips reached hers, so he kissed her cheek. "Do you want to come in?" She asked. Hoping he wouldn't notice her strange behavior.

He had, but pushed the thought aside. "Sure…Rory is something wrong?"

"No. Why?"

"I don't know. You just seem a little off."

"Well, I'm not…Do you want to start watching the movies?"

"Sure. What movies are we watching?"

"All three Lord of the Rings."

"Really?"

"Yeah. We haven't watched them in awhile, and I know how much you like them… Why don't you set it up while I go get the junk food?"

"Okay…Are you sure you're okay?"  
"Yeah. I'm fine." Rory said while walking into the kitchen. She returned to the living room about fifteen minutes later with two pizzas, lots of chocolate, cookie dough, red vines, and almost any other type of junk food you could think of.

Dean looked up at the pizzas in confusion. "When did you have time to order pizza?" He asked her. He still couldn't believe how much food she could eat. Even after dating her for two years.

"I ordered it before you got here. Did you set up the movies?"

"Yeah."

"Okay." Rory said as she put all of the food on the table, and sat down, trying to get as comfortable as she possibly could. The Lord of the Rings trilogy was really long, and she knew that they would be there for awhile. _'I hate The Lord of the Rings.'_ She thought. _'I've seen it way too many times.'_

By the end of the first movie Dean was absolutely sure that something was wrong with Rory. She hadn't made one sarcastic remark about the movie, which was really weird. She usually made so many comments that you could barely hear the dialogue. _'Yup something is definitely bothering her'_. Finally unable to take it anymore he asked, "Rory, are you sure your okay? You've been acting really weird since I got here."

"I'm fine." Rory answered. _'Am I really that obvious? Maybe I should just tell him now.'_

"You know you can tell me anything right?"

"Yeah."

"So tell me what's bothering you."

"It's nothing."

"Don't tell me that Rory. Something is definitely bothering you. You didn't make fun of the Lord of the Rings once. And every time I ask you if you're okay you get all defensive."

_'Okay. I have to do this now…He deserves better than this. Someone that loves him as much as he loves them.'_ Rory was about to break up with him, when she looked in his eyes. _'I can't do it._ _I can't hurt him.'_

Rory looked away and mumbled, "I uh, I forgot to get you a present." _'Oh great one Rory, like he's really gonna believe that.'_

"That's it? That's what's been bothering you all night?"

"Yeah."

"Well don't give it another thought. It doesn't bother me that you forgot to get me a present. You're here. That's good enough for me." Dean said relieved. He had been starting to get a little worried.

Dean left about 10 minutes after that. His mother had called letting him know that he was needed at home.

About an hour later Lorelai came home. She took one look at Rory, sat down on the couch, and said, "I'm never talking to my mother again."

"I take it dinner went badly?"

"Oh yeah. Bad doesn't even begin to describe how horrible dinner went. Think world war III."

"Hmm. Somehow I don't think it went that badly."

"You weren't there."

"That's only because someone didn't want me to come along and be a distraction... So, what happened?"

"It's a really long story."

"I have time."

"Okay fine, but don't say I didn't warn you."

"I'm waiting."

"Okay. Well…"

**_Flashback_**

Lorelai stood in front of her parent's house, putting off going in for as long as she possibly could. She really didn't want to tell them about what had happened with Christopher. So she drank her coffee really slowly and stared at the house, thinking about all of the horrible experiences that had happened to her while she had lived there. When she finished her coffee she reluctantly realized that she couldn't put it off any longer. With a sigh of defeat, she rang the door bell.

"Lorelai, nice to see you." Emily said as she answered the door.

"Oh. Sorry I'm late, Mom."

"No, don't be sorry. That's what the "warm" setting was invented for. Richard, Lorelai's here." She said stepping away from the front door.

"Um Mom, before we get the evening started and all, I wanna tell you something."

"Well, tell me outside."

"No, I'll just do it here."

"Why?"

"Oh there's something about standing near the exit. It's really working for me."

"You're being silly. You don't discuss things standing by a door. Come outside." Emily said taking hold of Lorelai's arm.

"I may have to take one more call tonight, Emily. Ben Stellen and I got cut off. Hello, Lorelai." Richard said, just coming out of his office.

"Well come outside with us until he calls back. Lorelai's about to tell us something."

"Oh perhaps that she's decided to buy an accurate timepiece."

"Now, Richard." Emily said, putting her arm through his and walking outside. "Is Rory okay?"

"Oh yes, Rory's fine. I'm fine. Everything's fine. It's really not that big a deal." Lorelai answered wanting to make this as short as possible.

"What would you like to drink?" Richard asked once they got outside.

"Oh, whatever."

"I can't read minds Lorelai."

"Well I really don't care, Dad. Whatever you have."

"We have everything Lorelai."

"All right. I'll have a Jagermeister and a Jell-O shot."

"Excuse me?"

"White wine."

"All right, sit." Emily said. Once they had all sat down she said, "Now, go ahead. Tell us."

"Okay, well-"

"Oh wait just a second. We brought you something from Martha's Vineyard." Emily interrupted.

"Oh that's great. But maybe we could just…" Lorelai started to say only to have Emily hand her a present. "I guess its present time."

"Open it." Emily said. Eager to see Lorelai's reaction to the present they had bought her.

"Scone mix. Wow!" Lorelai said with fake enthusiasm.

"This new little place opened down the road from our house and they make these wonderful scones. And that is their mix. So you can make them right in your own kitchen."

"Well thanks, Mom. I will put this right on the counter and stare at it for many years to come."

"You're not going to make them?"

"I'm not really much of a baker."

"But the instructions are right there on the bag."

"I know, but still"

"Still, what? Those are good scones."

"Hey. Maybe I'll give this to Sookie and she'll bake them."

"I don't understand why you simply can't follow the directions and make the scones."

"Rory would love those scones." Richard said joining the conversation.

"Okay, I promise. One way or another the scones will get eaten. That being said, can we please move on?"

"Fine go ahead, talk. We're listening." Emily said.

"Um. Okay, well. Um, it's about Christopher."

"Oh that reminds me." Emily cut in once again. "We got him a captain's hat. Richard where is that hat? Lorelai could bring it to him."

"No, I can't." Lorelai said before her father could get up and find the hat.

"Why not?"

"Well, it's just, um Chris and I aren't-"

"Aren't what?" Richard asked.

"They aren't together anymore, Richard."

"Why not?"

"I'm sure a vague reason is forthcoming." Emily said before Lorelai could answer.

"It just didn't work out, that's all."

"And there it is." Said Emily.

"I know you're disappointed-"

"Disappointed? Please. Lorelai, this is ridiculous. The two of you aren't in high school anymore." Emily cut in for the third time that night.

"I know."

"Emily, let's not talk about this."

"No, we are going to talk about it. You're running around like you have no responsibility in life. Like you can flit from thing to thing…"

"That's not true." Lorelai said trying to stick up for herself. She was sick and tired of her parents always blaming everything bad that happened, on her.

"…from man to man." Emily went on as if Lorelai hadn't said a thing.

"I don't flit from man to man."

"You have a daughter. This affects Rory, too. You know?"

"Emily you're wasting your breath." Richard said.

"I know this affects Rory. I'm not doing this lightly. In fact, I'm not doing anything at all!" Lorelai said, starting to raise her voice.

"There's no reason to raise your voice." Richard said.

"I can't believe this." Lorelai said in exasperation.

"I want to know why. I want a reason. I don't want any of this "just because" and "it just didn't work out" nonsense. I want a solid, adult reason why the father of my granddaughter and her mother can't seem to put a family together." Emily said determined to find out the true reason why Lorelai and Christopher weren't together anymore.

"His girlfriend is pregnant." Lorelai said. That shut both of her parents up for a second.

"What?" Emily finally asked.

"Sherry is pregnant. When Christopher found out, he went back to her. And that, Mother, is the reason."

"Are they getting married?"

"I don't know. Probably."

"Of course they're getting married." Richard said.

"How do you know?" asked Emily.  
"I know because I know Christopher. And Christopher always tries to do the right thing."

"The right thing is for him to be with his family. Lorelai and Rory are his family. He met this woman two minutes ago."

"Emily, he is going to be a father." Richard said starting to raise his voice.

"He already is a father!" Emily said also raising her voice.

"I really don't want to discuss this anymore." Lorelai said, interrupting her parent's argument.

"Lorelai, you have to talk to him."

"There's nothing to talk about."

"Tell him you want to get married."

"Okay Mom, please stop."

"Yes, Emily. Please, stop. You know that Lorelai never does anything unless she wants to no matter the consequences to anyone else." Richard said, getting up to refill his drink.

"What's that supposed to mean?" Lorelai asked hurt by her parent's behavior and reaction to what she had told them. It wasn't her fault Sherry got pregnant.

"Lorelai wants to be with Christopher." Emily said adamantly. "She told us that at the wedding."

"Yes. Now the wind has changed." Richard said.

"Excuse me?" Lorelai asked getting slightly frustrated.

"Christopher is fulfilling his responsibilities as he tried to do many years ago with Lorelai. And she turned him down and turned him away." Richard explained.

"I was 16." Lorelai said sticking up for herself, and what she had down all those years ago.

"If Christopher has found someone who will actually allow him to be a father to his own child, then of course that's what he's going to do." Richard continued to say as if Lorelai had never spoken.

"So you support this?" Emily asked appalled by the idea of Christopher being with anyone other than Lorelai.

"I understand this."

"I am appalled by you attitude!" Emily said to Richard.

"And I am shocked by your naïveté. Did you really expect this to work out? Did you really have pictures of Norman Rockwell family Christmases dancing in your head? Lorelai had her chance for a family. She walked away from it. That was her choice. He has a chance to be a father. I applaud him."

"Then you're an idiot." Emily said.

Lorelai left before she could here anything else. She couldn't believe her parent's had reacted to the news like this. They were talking about her as if she hadn't even been in the room.

_**End Flashback**_

"Wow…that was bad." was all Rory could think to say. She couldn't believe her grandparents had treated her mom like that.

"Yup." Lorelai agreed ready to change the subject. "I'm sick and tired of talking about what happened between Christopher and Sherry. Tell me something happy, like how your night went with Dean."

Rory didn't know what to say. _'Should I tell Mom about my decision to break up with Dean, and my feelings for Jess? What decision? I didn't even go through with it. I had the chance and I couldn't do it…maybe mom can help.'_

"Well?" Lorelai asked. "He didn't do anything to hurt you did he?" Lorelai asked suddenly.

"What? No of course not. I just…I- wow I don't know how to tell you this."

"You two didn't…" Lorelai started to ask hesitantly.

"What? No! I think I should break up with him!" Rory said. She didn't even want to think about what her mother had implied.

"Where did this come from? I thought you loved Dean." Lorelai asked completely confused.

"I did. Or at least I thought I did. It's actually a really long story."

"I have time. All night in fact."

"Um…I don't know where to start."

"Why don't you start at the beginning? When you started to question your feelings for Dean."

"Mom if I tell you this, you have to promise me that you'll listen, and you won't interrupt."

"Okay. I promise. Now spill!" Lorelai said, curious to find out what had brought about this change.

"Honestly, I've been questioning my feelings for Dean for a really long time. I think it started when Jess came to town-"

"Rory are-"

"Mom, you promised you wouldn't interrupt."

"Sorry." Lorelai said, putting her hands up in surrender.

"It's okay. Anyways, after I met Jess I felt this instant connection with him. The more I got to know him, the more I realized we had in common. Before I knew it I found myself liking him as more than a friend, which I tried to deny. And I did, until Sookie's wedding."

"What happened at Sookie's wedding?"

"Jess showed up."

"Jess wasn't at Sookie's wedding."

"Yeah he was. He had just come back and he came to see me."

"Okay, so he crashed Sookie's wedding, and?"

"And we kissed."

"You kissed, like you kissed?"

"Yes."

"Who kissed who?"

"What does that matter?"

"Because it matters. Did he kiss you? Did you kiss each other? Did you trip and your faces accidentally-"

"I kissed him."

"Okay…What does Dean think about this?"

"I haven't told him yet."

"Is this the reason that you want to break up with him?"

"It's part of the reason. Look, while I was in Washington I realized how much I liked Jess and wanted to be with him. And the only way I can do that is if I break up with Dean."

"Then why didn't you?"

"I don't know. I had it all planned out, well kind of. I didn't really know what I was going to say, but that's not the point. The point is, I took one look at his face and I just couldn't do it. I couldn't hurt him."

"Rory, you're gonna have to, unless you want to spend the rest of your life pretending that you feel a certain way about someone when you really don't. Dean deserves better then that. You deserve better then that."

"I know. You're right." Rory said.

"Are you sure about Jess?"

"Yes, Mom he's not as bad as you think he is. He's actually a really good guy."

"Alright. I guess if you sure." Lorelai said reluctantly.

"I am. Mom, I don't want you to hate this. Will you promise me that you'll give him another chance?"

"Yeah, I guess. But if he hurts you I swear I'm gonna-"

"Thanks mom." Rory said cutting her mom off before she could go on any further. "Mom?"

"Yeah?"

"What if Jess doesn't feel the same way about me?"

"If Jess doesn't like you then he's an idiot. Didn't you guys talk after the kiss?"

"No." Rory said sheepishly. "I left before we had the chance to, but I wrote him a letter."

"Did you send it?"

"Yes, two weeks after I got to Washington."

"And he didn't write you back?"

"Nope."

"Well, there's only one way for you to find out how he feels about you."

"What?"

"Talk to him." Lorelai said. A minute later Rory got off the couch, grabbed her coat, and headed to the door. "Rory? Where are you going?"

"I'm gonna go break up with Dean, and then I'm gonna find Jess and get this all sorted out."

"Okay. Don't be out too late."

"I won't." Rory said as she walked out the door.


	5. Chapter 5

**Undecided:**

**Disclaimer: I don't own Gilmore Girls or anything related to it.**

**a/n: Sorry I haven't updated in awhile. I've been really busy with school, homework, etc. Thanks for all of your reviews. They've been a huge inspiration for me to continue this.**

**Ch.5**

Rory stood in front of Dean's house wondering how she was going to do this. She had been determined to break up with Dean after her talk with her mother, but now she was loosing her nerve. Saying she was going to break up with him and actually doing it were two completely different things. She knew she didn't love him anymore, and that breaking up with him was the right thing to do, but she didn't know what to say or even how to go about it. She'd never broken up with anyone before, and didn't want to say anything that would hurt him too badly. Looking down at her watch she realized that it was 11:30. She'd been standing out there thinking for longer than she thought.

_'He's probably sleeping now. Maybe I should just wait till tomorrow…No but I can't! I have to break up with him now because if I don't, I don't think I ever will.'_ With that thought in mind she climbed up the tree next to his window and tapped on it softly. About a minute later it opened and Rory climbed through it and into his room.

"Rory?" Dean said sleepily. "What are you doing here?"

"Um. I- ah- I wanted to talk to you."

"Couldn't it have waited until tomorrow?"

"No. It's important…It's about us."

Dean woke up completely when he heard that statement. "What about us?"

"Ithinkweshouldbreakup." Rory mumbled quickly.

"What?" Dean asked confused. He hadn't understood a word she had said.

"I think we should break up." Rory said more slowly.

"What? Why? Is this because of HIM?" Dean asked getting angrier by the second.

"Who?"

"Do I really have to spell it out for you?" Dean asked. He couldn't believe she was doing this to him. After everything every thing they'd been through, all of the crap with Tristan, their first break-up, getting back together, admitting their love for each other, etc. He just couldn't believe that she was doing this now. He thought she loved him, but apparently she didn't because she was breaking up with him to be with Jess. Just the thought of her being with that guy pissed him off beyond belief.

"Yes. Dean, look I'm trying to understand you but you're not making any sense."

"JESS!" Dean yelled.

"What? NO! This has nothing to do with Jess."

"Oh please. You've been into him since he got to town!"

"No I haven't."

"Oh really? So are you telling me that you feel nothing for him?"

"…" Rory didn't say a word.

"That's what I thought."

"Dean-"

"You should go." Dean said turning his back on her.

"Dean…I'm sorry. I never meant to hurt you."

"Well. You did."

Rory started to walk towards the window, but stopped. "Dean. Do you think that we could be friends again someday?"

Dean hesitated for a second before saying, "I honestly don't know. Maybe someday." With that Rory climbed out of his window and out of his life forever.

**Sorry it wasn't longer, but like I said before, I haven't had much time to write…Don't forget to review. Thanks :)**


	6. Chapter 6

**Undecided:**

**Disclaimer: I don't own Gilmore Girls or anything related to it. If I did Jess would never have left in the first place, and Rory never would have slept with Dean, or dated Logan.**

**A/N: Sorry I haven't updated for awhile. I had a huge writers block and couldn't figure out what to have happen next, not to mention I had tons of homework. School really sucks! Anyways I hope you like this chapter…It was really hard to write. **

**Ch. 6**

**11:30 that night:**

Jess sat at the bridge attempting to read 'Oliver Twist' for the millionth time that night. It was no use. He couldn't concentrate. Every time he read this book he would think about Rory, and that night.

He had just had an argument with Luke and had gone out to get some fresh air when he looked up and saw her. She was coming out of Doose's Market. Without even thinking he had gone over to her.

She was different then anyone he had ever met, not to mention she was the only sane person in this crazy town. He hadn't known her for that long, but he felt like he could trust her, as strange as that sounded. These thoughts and others soon led to the amazing kiss they had shared at Sookie's wedding. Sure he had kissed people before. Hell, he had gone a lot further than that, but it had never mattered. He had never actually cared about the other person. But with Rory it was different. She was different, special. He cared about her, a lot. He had to, to move back to this crazy, town.

**Flashback**

_**'**I can't believe I'm doing this.'_ Jess thought as he walked out of Luke's Diner to look for Rory, not that he would admit that to anyone. He had done the unthinkable. He had moved back to Stars Hallow. _'This is crazy!'_ He couldn't believe he had actually moved back. He hated this town, but he had come back for her. _'When did I get so sentimental?' _

Before he knew it he was there, at Sookie's wedding. When he looked up he saw Rory talking to some guy he had never seen before. He knew the exact moment she saw him. She froze before hesitantly walking over to him.

"What are you doing here?"

"Hello to you, too."

"Is everything okay?" she asked him worriedly.

"You look nice." _'That was the biggest understatement of the year. Nice doesn't even begin to describe how she looks.'_

"Thank You. What are you doing here?" Rory asked looking really confused to see him there.

"I moved back."

"What?"

"I moved back."

"But – what – why?"

"Just wanted to." I replied.

I really didn't feel like trying to explain something I didn't fully understand myself. The next thing I knew Rory was kissing me. ME! Jess Mariano. I just couldn't believe it. I had been waiting for something like this to happen since almost the moment I met her. And man was it something. It was the best kiss I had ever had. Unfortunately before I could get too into it Rory pulled away.

"Oh my God! Oh my God!" She said.

"Rory-" I tried to say something, anything to calm her down. She looked really freaked out.

"Don't say a word!"

"Okay." I said.

"I have to go." Rory said running away. Before she disappeared from my sight she turned around and said, "Oh, welcome home!" She was gone before I could come up with a reply.

**End Flashback**

Jess took a deep breath and looked out over the bridge. _'I wonder if she'll do it. I wonder if she'll actually break up with him.' _He had been about to move on. After she left without saying a word to him he thought that she regretted the kiss. Not able to stand that thought he had decided to try and forget about her. It was around that time that he noticed this girl. Share? Stacy? Her name wasn't important. He had been about to hook up with her when he got Rory's letter.

Jess reached into his pocket and pulled out the letter.

"_Dear Jess,_

_Wow! I really don't know what to say. What do you say to someone after you kiss them while you have a boyfriend…I guess I should just be honest. Do you remember the kiss at Sookie's wedding? I sure do. I know that you're probably expecting me to apologize, but I can't. You see, I enjoyed it. And I'm not sorry that it happened. I'm just sorry that it happened under the circumstances that it did (with me still being with Dean.) But you won't have to worry about that for long. I plan to break up with him as soon as I get back to Stars Hollow. I don't know how I will but I will. Is there any way to break up with someone without hurting them? Because I really don't want to hurt him. He's always been there for me, and he doesn't deserve to get hurt. Not by me…But enough about Dean. Dean isn't the point of this letter. You are. You see I like you, a lot. I have for a long time. I was just too scared to admit it. But I'm admitting it now: I like you Jess Mariono. I know that you probably don't feel the same way about me, but I thought you should know. I just hope that you knowing this won't affect our friendship if you don't feel the same way about me._

_Rory _


	7. Chapter 7

**Undecided:**

**Disclaimer: I don't own Gilmore Girls. If I did then Jess never would have left, and Rory wouldn't have slept with Dean or dated Logan.**

**Ch.7**

_'I did it! I actually broke up with Dean.'_ Rory couldn't believe that she had gone through with it. _'Why do I feel like such a jerk?' _Despite her relief at having it over with, she couldn't help but feel a little sad. Her and Dean were completely over. No matter what she did, she couldn't forget the look on his face. He had looked so…heartbroken, and that look had only intensified when he realized that she wanted to be with Jess. _'I hope he'll be able to forgive me someday.' _Dean was a good guy- despite his jealousy and over-protectiveness. She didn't want to lose his friendship.

_'I wonder what Jess is doing?'_ Just the thought of him made her feel lightheaded, excited, happy, nervous, etc. She couldn't help but wonder if he had received her letter. She was anxious to find out what he thought of it.

'_Does he feel the same way about me as I feel about him?'_ Rory didn't know what she would do if he didn't. _'Why did I send that letter in the first place? I'm going to be so embarrassed if he doesn't have any feelings for me beyond friendship. Oh my God! What am I going to do if he doesn't like me? How will I face him? Why would he like me anyway? Jess could have any girl he wants: a more experienced girl. Why would he want to have anything to do with me?' _Without even realizing it, Rory had walked to their spot: the bridge. She froze when she saw the figure sitting there.

"Jess…"

Jess looked up at her and quickly stuffed her letter back into his pocket. "Rory."

"Hi." She said, taking a seat next to him.

"Hi." It was silent for a couple of seconds. "How was Washington? Did you do anything exciting?"

"No. Not really…What about you? How was your summer?"

"Boring." They didn't say anything after that for about five minutes.

"So…" Rory started to say, unable to take the silence any longer. "Did you get my letter?"

"Yeah."

"Okay." Rory said fearing the worst. She was so caught up in her thoughts that she didn't notice Jess moving until he was holding her hand. Startled, she hesitantly brought her eyes up to his. His face was only an inch away. _'When did he get so close?'_ "And?" she whispered. If she moved her head even a little their lips would touch.

"I like you too." Jess mumbled as he closed the distance between them, and kissed her. He pulled away a second later. "What about bagboy?"

"I broke up with him."

"You did?" Jess doubtfully asked.

"Yeah. Right before I came here and ran into you…Why? Did you think I wouldn't?"

"The thought did cross my mind."

"Jess, I said I would break up with Dean, and I did."

"So…You're officially broken up with Dean."

"Yeah. I'm officially broken up with Dean."

"Good." He smirked as he leaned in to kiss her again.

**Twenty Minutes Later**

"I should probably get home." Rory whispered, pulling away from an intense kiss.

"No. Stay awhile longer." Jess said, leaning in to kiss her again.

Rory reluctantly pulled away at the last second. "I can't. It's getting late. My mom is probably freaking out as it is."

"Yeah. I should probably head back too, before Luke notices that I'm gone."

"You snuck out?" Jess didn't answer. He just looked at her innocently. "Jess!" Rory exclaimed, playfully hitting his arm.

"What?"

"I can't believe you snuck out."

"It's not that big a deal." Jess said looking deep into her eyes all joking gone.

"Jess?"

"Yeah."

"What are we exactly? I mean are we boyfriend and girlfriend or-"

"We're boyfriend and girlfriend." Jess cut her off before she could ramble on further. "That is if you want to be," he added a second later, looking unsure of himself for the first time that night.

"I do."

"Good."

"So we're dating."

"Yup."

"Okay…I'll see you tomorrow?"

"Yeah." Jess mumbled. He couldn't believe that they were together, and Rory was finally his.

"Okay. I'll see you then." Rory said as she lightly kissed Jess on the lips before walking away, and going home.


	8. Chapter 8

**Undecided**

**Disclaimer: I don't own Gilmore Girls or anything related to it. If I did then Jess never would have left, and Rory never would have slept with Dean or dated Logan.**

**a/n Thank you again for all of the reviews. I'm glad you all like it.**

**Ch.8**

"Rory!" Lorelai called in a singsong voice for the fifth time that morning.

"Go away!"

"It's time to get up."

"Too early." Rory said, rolling over and unsuccessfully trying to go back to sleep.

"Well then. I guess you don't want any coffee."

"I'm up. I'm up." Rory reluctantly sat up in bed, and took the cup of coffee from Lorelai's hands.

"Hey! That's mine."

"Not anymore. You woke me up so now you have to pay the consequences."

"Man, you're grumpy in the morning."

"Only when someone wakes me up."

"Well, sorry! I just wanted to ask you how last night went."

"Last night?"

"Yeah. Did you break up with Dean? Or did you chicken out again?"

"I broke up with Dean."

"How did he take it?" Lorelai asked while sitting on the bed next to Rory.

"As good as can be expected…I guess."

"Meaning?"

"He was really mad. He got all defensive and asked if breaking up with him had anything to do with Jess-"

"Which it did."

"Well yeah, in a way, but not completely. I would have broken up with Dean even if I didn't want to be with Jess. Don't get me wrong. Dean is a really nice guy. He's just not the guy for me."

"And you think Jess is…"

"I don't know…maybe."

"So I take it you and Dean aren't friends."

"Not right now, but hopefully we will be if he can ever forgive me."

"He will. Just give him some time. So, are you and Jess-"

"Together? Yeah."

"You sure don't waste any time!"

"Hey!"

"What? I was just stating a fact. I mean you broke up with Dean last night, and now the very next day, you're already with Jess. How did that happen by the way? Did he get your letter?"  
"Yeah, he got my letter."

"And?"

"And he likes me too." Rory had never looked so happy in her life. She just couldn't stop smiling, a fact the Lorelai couldn't help but notice.

"I told you so."

"Yes you did."

"You look really happy."

"I am."

"I've noticed. You haven't stopped smiling since we started talking about Jess."

"I'm not smiling."

"Oh really? Then what do you call what you're doing now?"

"Okay fine. I'm smiling…I can't help it. I've never felt this happy before."

"Not even when you had your very first cup of coffee?"

"Not even then."

"Wow!"

"There is just something about Jess-"

"You mean besides his charming personality?" Lorelai sarcastically asked.

"Oh shush you! I'm trying to open up here and tell my best friend how I'm feeling, and you're mocking me!"

"Am not!"

"Are too!"

"Am not!"

"Are too!"

"Am not!"

"Okay. This is ridiculous. Just admit that you were mocking me!"

"How can I admit to doing something that I wasn't doing?"

"Mom!"

"Okay fine! I was mocking you. Are you happy now?"

"I little."

"Okay. I admitted to mocking you now go on with the rest of your story."

"No."

"Why not? Now I'm curious. What is it about Jess that makes you so happy?"

"Oh look at the time…" Rory casually got out of bed, stretched, and walked into the kitchen.

"Lorelai Gilmore, get back in here this instant!"

"I can't. I'm meeting Lane."

"In your pj's"

"No."

"Then come back in here. You can tell me all about Jess while you're getting ready. Besides you never really answered my question."

"What question?"

"How did you and Jess get together? All you said was 'we're together.' "

Rory immediately walked back into her room, and went to her closet to find something to wear. "I ran into Jess at the bridge right after I broke up with Dean. We talked, found out we like each other, and now we're together. End of story."

"You know I really feel like I was there. Oh don't wear that!"

"Why not?"

"Because it makes you look like you're five."

"So, it's just Lane."

"Have I taught you nothing? What if you run into Jess on the way? Do you really want to be caught wearing that?"

"No. You're right."

"Of course I'm right. I'm always right."

"Alright 'Miss I'm always right'. If I shouldn't wear this then what should I wear?"

"Hmm…Good question." Lorelai walked over to the closet, and started looking around. A minute later she picked out a nice comfortable pair of jeans, and a blue form-fitting shirt. "This."

"How do you do that?"

"Do what?"

"Find something to wear in two seconds?"

"Lot's of practice. What time are you supposed to meet Lane?"

"10:30."

"Isn't it 11:00?"

"Oh no! I'm late!" Rory frantically ran around the room trying to get ready. "I'll talk to you later mom." Rory said as she ran out of her room.

"Hun?"

"Yeah?"

"What do you say we go shoe shopping when you get back?"

"Okay. See you later!"

"Bye!" Laughing Lorelai shook her head, and walked into the kitchen. She would never get tired of watching her organized daughter run frantically around the house.


	9. Author's Note

**Hey guys,**

**I'm really sorry that I haven't updated in awhile. I'm having a huge writer's block. If anyone has any ideas about what should happen next let me know. Also, Do you think that Lane should be supportive of Jess and Rory's relationship? Or should she be against it? **

**-jrforever**


	10. Chapter 9

**Undecided:**

**Disclaimer: I don't own Gilmore Girls.**

**a/n Thank you ****Curley-Q, hollowgirl22, RogueHoney for your wonderful reviews and ideas. I don't think that I would have finished this chapter without them. **  
**  
Ch.9**

"I'm so sorry I'm-" Rory was abruptly cut off by Lane who immediately ran up to her and gave her a huge hug.

"You're back! You're never leaving me again. I missed you so much!"

"I know! I missed you too."

"I don't know how I survived the summer. I mean I've always known that everyone in this town was a little crazy, but I didn't realize how much until you were gone… I'm so sorry that I couldn't talk to you longer yesterday. Momma set me up with this potential Korean doctor. It was horrible! He spends all of his time studying. Oh and in his free time he listens to classical music! Classical! Who listens to classical music anyway?"

"So I take it your night sucked?"

"Sucked doesn't even begin to describe it. Last night was one of the worst set ups in history. Even that guy that I had to go to that hayride with was more interesting and we barely even talked."

"Wow."

"Yeah…So how was Washington?"

"It was okay. I roomed with Paris."

"I'm sorry. How did that go?"

"Surprisingly well, believe it or not Paris actually went on a date."

"Really?"

"Yeah"

"Um, no offense, but who would want to date Paris?"

"I know! That's exactly what I thought, but Jamie really seemed to like her."

"So are they together now?"

"Yup"

"Wow…"

"I know. It's unbelievable isn't it?"

"Yeah…So what did you want to talk about yesterday? You sounded really worried when you called. Are you okay? You didn't get hurt or anything when you were in Washington did you?'

"No. I'm fine."

"Then what was wrong?"

"Nothing was wrong exactly…" _'Should I tell her that I broke up with Dean now? Or should I wait? I should probably tell her now. I don't want her finding out from someone else, and knowing this town everyone will probably know by the end of the day.'_ Taking a deep breath Rory said, "IbrokeupwithDean."

"What?"

"I broke up with Dean."

"What? Why? And when did you break up with him? Why didn't you tell me sooner? Did you break up with Dean while you were in Washington? When-"

"Lane, calm down. Breathe."

"I am. I just-"

"I broke up with Dean because I realized that we weren't meant to be together, as clichéd as that sounds. I wasn't happy anymore. Honestly I can't remember the last time we just hung out and talked without fighting-"

"But isn't fighting a normal part of a relationship?"

"Yeah, but not like that. I think that what really broke us up was his lack of trust in me. He would get jealous whenever I talked to another guy. It was like he thought that I was going to cheat on him or something. I just couldn't live like that anymore."

"But I thought you loved him."

"I used to think I did too, but I don't. I don't think I ever really did. Honestly, the only reason I said that I did was because I knew that that was what he wanted to hear. It was either say I love you or break up with him for good. At the time I wasn't ready for that so I said the only thing I could to stay with him."

"When did you realize all of this?"

"About a year ago, I was just too scared to admit it. Actually it all started around the time that Jess moved to town…"

**Awhile Later:**

"Wow! So you and Jess?"

"Yup, me and Jess…"

"Wow…I don't really know what to say. Are you sure-"

"That I want to be with him? Yeah. I'm positive. It's different with Jess. When I'm with him I feel like I can be me. I don't have to pretend to be something that I'm not. He gets me, and for some reason he likes me, which makes no sense at all. Jess could have any girl that he wanted, a more experienced girl, but for some reason he chose me."

"Rory, Jess would be crazy if he didn't like you. To be honest I've known that he's liked you for a long time now."

"Why didn't you tell me sooner?"

"You were with Dean. I just figured that it would complicate things more then they already were…So did you really kiss Jess at Sookie's wedding?"

"Yeah."

"And?"

"And what?"

"How was it? Was it good? Cause he looks like he would be a really good kisser, not that I would know or anything considering the fact that I've never kissed a guy in my life."

"Lane!" Rory embarrassingly exclaimed.

"What? You know that I can't experience these kinds of things for myself, so I live them through you. So with that in mind I repeat, was it good?"

"It was unbelievable." Rory blushingly replied. They broke into uncontrollable giggles seconds later.

Once they had settled down Lane seriously asked, "Rory? Are you really sure that you want to do this? Be with Jess I mean?"

"Yeah. I'm sure."

"Okay."

"Lane. He's not as bad you think he is. I know he acts like he's this cool, tough guy that doesn't give a damn about anything, but he's not. When you look underneath all of that he's this really nice, funny, considerate, and sarcastic guy. I think that you guys could be really good friends if you gave him half a chance."

"Rory I don't know if I can. I mean he trashed your car, and he's the reason that you sprained your wrist."

"Lane that was ages ago. And that accident could have happened to anyone. It probably would have happened whether Jess was there or not. Look could you just give him a chance? For me? Just talk to him. Try to get to know him. If you do then I think that you'll see what I do."

"I don't know…"

"Come on. Just try it for a little while? A month?"

"You're pushing it."

"Okay then, a week? Come on Lane please? Just try it for a week and if you still hate him after that then fine. I just think that he deserves a chance."

"Okay fine." Lane reluctantly said.

"Thank you so much Lane. You're the bestest friend in the world. I promise you that you won't regret this."

"So what are you doing later?"

"I'm going shoe shopping with my mom. You want to come?"

"I wish I could, but unfortunately I have another date with that extremely boring potential Korean doctor."

"I'm so sorry. You want me to bring you back something?"

"Of course… Oh no! What time is it?"

Rory looked down at her watch and replied,"It's 12:30. Why?"

"Oh no! I hate to say this but I really have to go. Momma found this new soy recipe and wants me to help her make it. Call me when you get back?"

"Sure. You should probably go before Mrs. Kim freaks out and sends a search party after you."

"Yeah you're probably right. See you later?"

"Yeah. Good luck with your mom and that date!"

"Thanks, I'm gonna need it." Lane said before hugging Rory and running home.

* * *

**Sorry Jess wasn't in this chapter. I didn't have that much time to write it. I'll try to have him in the next chapter. Please review and let me know what you thought. **

**-jr forever**


	11. Chapter 10

**Undecided:**

**Disclaimer: I don't own Gilmore Girls**

**Merry Christmas!**

**Ch.10**

'_Well, that went better than I thought it would. I can't believe that Lane actually agreed to give Jess a chance…'_ Rory was so deep in thought that she didn't hear Jess come up behind her.

"Hey" Jess said, wrapping his arms around her from behind.

Rory instantly tensed until she realized who it was. "Hey," she replied, relaxing into his embrace.

"Something wrong?"

"No, I just wasn't expecting anyone."

"Oh…Do you want me to go?"

"No. I'm really happy that you're here."

"Good," Jess mumbled before he started to lightly kiss her neck.

Rory tilted her head to the side to give him more room before she came to her senses and pulled out of his embrace.

"What's wrong?" Jess asked, worried that he had done something wrong.

"Nothing."

"Then why are you standing all the way over there?"

"…"

"I knew this was too good to be true." Jess said too quietly for Rory to hear.

"Can I talk to you for a second?" Rory nervously asked.

"Sure."

"Alone?"

'_This must be really bad if she wants to talk to me alone.'_ Jess looked around but didn't see anyone nearby. "No one's here," he said after a second.

"I know, but someone can walk by at anytime and-"

"I know a place we can talk." Jess said taking her hand and leading her to the area behind Luke's Diner. Hardly anyone ever went over there. Once they got there he let go of her hand, and put his hands in his pockets, waiting for her to start the dreaded conversation. When she didn't say anything after a couple of minutes he asked, "So…What did you want to talk about?"

Rory didn't say anything. She didn't know how to say what she wanted to say.

'_She probably regrets what happened last night…I was an idiot to think that she would ever really want to be with me." _Jess thought taking her silence the wrong way.

"I get it." He tensely said a moment later.

"Get what?"

"You regret what happened last night and want to break up with me, right?" Jess nonchalantly replied trying to act like that thought didn't affect him in the least.

"What? No! That's not it at all!"

"It's not?" Jess asked slightly relieved.

"No."

"Then what's going on?"

"I think that we should wait awhile before we tell everyone that we're dating," Rory quickly said. She couldn't believe that Jess had thought that she wanted to break up with him. That was the furthest thing from the truth. If anything, she figured that he would be the one to want to break up with her.

"Are you that ashamed to be with me?" Jess whispered. He normally didn't show people this side of him. The vulnerable part that only wanted to be loved and appreciated, but he couldn't help it. This was the only girl that he had ever really cared about. He couldn't stand the thought of her being ashamed to be seen with him, although he couldn't really blame her. He wasn't really the best of people, why would she want everyone to know that they were together?

Rory had never seen Jess look this vulnerable. He was usually so sure of himself. Without another thought she put her hand on his cheek and said, "I could never be ashamed of you Jess. I just think that we should wait awhile before we flaunt our relationship in front of everyone. I mean, I just broke up with Dean yesterday."

"So this is about Dean? He's a big boy Rory. He can take care of himself."

"I know. I just think that we should give everyone a little time to get used to the fact that Dean and I are over before we tell them about us."

"How much time are we talking about here?"

"I don't know…Don't you think we should let everything settle down first?"

"I guess…" Jess reluctantly agreed. "Just don't wait forever k? I don't want to hide our relationship at all, but if that is what you want to do then I guess we can."

"I don't want to hide our relationship either. I just think that it would be best for everyone if we waited awhile…"

Before Rory could finish her sentence they heard Luke say, "Jess! Your breaks up. Get back in here!"

"I should probably go." Jess said, rolling his eyes at his uncle's antics.

"Yeah. We're good right?"

"Yeah, we're great," Jess said before he lightly kissed Rory on the lips. He turned to go, but before he could get very far, Rory grabbed his hand and pulled him to her. She wrapped her arms around his neck and leaned in until there lips were touching once again. Jess forgot about everything the moment he felt Rory's lips on his. There was just something about kissing Rory. It was unlike anything he had ever experienced before.

The kissed remained chaste until Rory shyly put her tongue on Jess' lips, asking for entrance. She had never kissed anyone like this before. She had kissed Dean, but their kisses had always remained completely innocent. She wanted it to be different with Jess.

Jess was shocked when he felt Rory's tongue on his lips, but he quickly got over it, and let her in.

Before they could go any further they heard Luke impatiently yell, "Jess! Get your ass back in here. The diner can't run itself!"

"You should probably go," Rory whispered, reluctant to let go of Jess.

"Yeah…" He replied. He didn't want to let go of Rory. Not after he had finally gotten her.

"Jess!" They heard Luke call for the millionth time.

Rory reluctantly let go of Jess. "See you around?" She shyly asked suddenly feeling embarrassed by her earlier behavior.

"Yeah," Jess said before kissing her cheek. "Do you want to hang out later?"

"I would love to, but I'm going shoe shopping with my mom…"

"Oh. Okay…"

"Jess!" They heard Luke call once again.

"I gotta go."

"All right…Call you later?"

"Sure," Jess said before turning and walking around the corner and back into the diner.

* * *

"Lucy I'm home!" Rory cheerfully called as she opened the door and walked in the house.

"Upstairs!" Lorelai called back.

"What is that horrible smell? It smells like something is burning…Please tell me that you didn't try to cook."

"Oh no! The food!" Lorelai said, running down the stairs and into the kitchen.

"You tried to cook?"

"I didn't actually make it. Sookie did. I just put it in the oven to heat it up." Lorelai said as she took the burned remains of some unrecognizable dish out of the oven. "There. It's not that bad."

"It's black" Rory said.

"Way to state the obvious."

"Yup"

They looked at each other and burst out laughing.

"I'm the worst cook in the world." Lorelai said in between giggles. "I couldn't even remember to take it out of the oven."

"I could of told you that."

"Hey! You weren't supposed to agree with me." Lorelai exclaimed pretending to be offended. "So are you ready to go shopping?" Lorelai asked after she threw the food away.

"Of course! I'm always ready to go shopping."

"I've taught you well. Never turn down an opportunity to shop, unless of course it's with my mother. In that case turn it down immediately. There is nothing worse than shopping with my mother."

"I'm sure it's not that bad."

"Did I ever tell you about that time when I was ten and…"

* * *

Five hours, and twenty shoes later…

"I can't believe you bought that." Rory said as they exhaustedly plopped down on the couch.

"Bought what?"

"That hideous pair of shoes that you're never going to wear."

"I'll wear them!"

"They're puke yellow!"

"They were on sale."

"But they're puke yellow!"

"So?"

"Those are the ugliest shoes I have ever seen! I can't believe you wasted our hard earned money on them."

"I would hardly call five dollars a waste."

"It is if you aren't going to wear them."

"So…How did it go with Lane earlier? You never told me."

"It went surprisingly well. Lane agreed to give Jess a chance!"

"No way!"

"Way!"

"Did you force her into it?"

"No! Of course not!"

"Ah, so you guilted her into it"

"I did not!"

"Right…"

"I didn't!"

"I'm sure…So did you run into Jess like I said you would."

"Yup."

"And?"

"And what?"

"What happened?"

"You really want to know?"

"Yeah, I wouldn't ask if I didn't."

"It went really good."

"That's it? That's all that you're going to tell me?"

"Well what else do you want to know?"

"Did you kiss? Talk? Are you still together?"

"We kissed a little…" Rory said beginning to blush.

"And?"

"We agreed to keep things quiet for awhile."

"Jess actually agreed to that?"

"Yup."

"Wow! I'm shocked."

"Why?"

"He just doesn't seem like the kind of guy that would want to keep something like that quiet."

"Well, he didn't want to-"

"That doesn't surprise me."

"Mom!"

"What?"

"I thought you said that you were going to give him another chance."

"I am. I just don't want you to get hurt."

"I won't."

"How can you be so sure?"

"I can't. I just know. Jess would never do anything to hurt me…"

"Just promise me that you'll be careful?"

"I'll be careful."

"Okay. So, do you want to watch a movie?"

"Actually I was planning on calling Jess…"

"Oh…"

"I promised him I would call him when we got back. Are you okay?"

"Yeah, I'm fine.

"Sure?"

"Yeah, don't worry about me."

Rory looked at her mom closely. She could tell that something was wrong, but she didn't know what.

"Go ahead. Go talk to your boyfriend." Lorelai assured Rory.

"Okay, if you're sure…"

"I'm positive."

"Okay. I'll be in my room if you need me," Rory said while picking up the phone and walking into her room. She quickly dialed his number, hoping that Luke wouldn't answer.

"Hello?" Jess said, answering the phone.

"Hey."

Jess smiled recognizing her voice in a second. "How was the shopping?"

"It was great…"


	12. Authors Note

I'm so sorry that I haven't updated in such a long time! I didn't mean to let so much time go by between the last chapter. To be honest I have no idea where this story is going anymore. I've started writing the next chapter but I just can't seem to finish it. I've been having a huge writer's block. I know that I've asked this in the past, but if anyone has any ideas or suggestions please let me know.

Email me at: s e l e n a 7 0 6 y a h o o . c o m (there is an underscore between the 7 and the 0. wouldn't let me post it.)  
or ym me. My ym is: jessandrorylover :)

I hope to hear from you soon!

jr forever


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